Tertiary amine oxidation and products thereof

Abstract

Tertiary amines in which at least one group bonded directly to the nitrogen atom is alkyl of 2 to 20 carbon atoms or in which two or more groups bonded directly to the nitrogen atom together are alkylene of 4 to 7 carbon atoms, are oxidized by trihaloacetyl anhydride or trihaloacetyl halide to mono- and di-trihaloacetylated alpha, beta-enamines.

What is claimed is: 
     
       1. The method of oxidizing a tertiary amine selected from the group consisting of triethyl amine, diisopropyl ethyl amine, and N-methyl piperidine to form an acylated enamine, which method comprises mixing said amine with trihaloacetic anhydride or trihaloacetyl halide in a solvent inert to the reactants at a temperature from 0° to 100° C., and separating beta-trihaloacetylated alpha, beta-enamine from the reaction mixture.   
     
     
       2. The method as claimed in claim 1 in which the trihalo group is trifluoro and the halide is chloride. 
     
     
       3. The method as claimed in claim 1 in which additional inorganic base is added to the reaction mixture. 
     
     
       4. The method as claimed in claim 2 in which said amine is mixed with trifluoroacetic anhydride at a temperature from 0° to 25° C. 
     
     
       5. The method as claimed in claim 4 in which additional inorganic base is added to the reaction mixture. 
     
     
       6. The method as claimed in claim 5 in which said inorganic base is sodium hydride. 
     
     
       7. Mono- and di-trihaloacetylated alpha, beta-enamines made in accordance with the method of claim 1. 
     
     
       8. The method as claimed in claim 1 in which said tertiary amine is triethyl amine. 
     
     
       9. The method as claimed in claim 1 in which said tertiary amine is diisopropyl ethyl amine. 
     
     
       10. The method as claimed in claim 1 in which said tertiary amine is N-methyl piperidine.